HCID 14987158, compound → HCID 14987159, compound

HRID 2051520Notes

Reaction equation

HRID 2051520 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C@H:14]([N:17]([C:25](=[O:28])[CH2:26][CH3:27])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[C@H:13]([CH3:29])[CH2:12]1)=O)C1C=CC=CC=1>CO.C(O)(=O)C.[Pd]>[CH3:29][C@H:13]1[C@@H:14]([N:17]([C:25](=[O:28])[CH2:26][CH3:27])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[F:24])[CH2:15][CH2:16][NH:11][CH2:12]1

Participants

5

Reactant 1

HCID 14987158HCID 14987158, compound

Product 1

HCID 14987159HCID 14987159, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of cis-1-benzyloxycarbonyl-3-methyl-4-[(1-oxopropyl)-2-fluorophenylamino]-piperidine (576 mg, 1.45 mmol) and 10% Pd-C (100 mg) in methanol (25 ml) and acetic acid (5 ml) is hydrogenated at 50 psi for five hours. The reaction mixture is filtered through celite and the filtrate is concentrated. The residue is diluted with ethyl acetate, basified to pH 11 with 2N NaOH and shaken. The separated organics are dried over sodium sulfate and concentrated to give cis-3-methyl-4-[(1-oxopropyl)-2-fluorophenylamino]piperidine as an oil: 333 mg; 87%.

Workup

  1. filtrationThe reaction mixture is filtered through celite
  2. concentrationthe filtrate is concentrated
  3. additionThe residue is diluted with ethyl acetate
  4. dry with materialThe separated organics are dried over sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-79e489281e534ed08797b1ff6e844486
Source dataset
uspto-grants-1991_05
Patent number
US05019583

Reaction notes

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